His Winning Personality (Pun Crack Fic)
by Random.Inked.Thoughts
Summary: Dean's fail safe how to date an angel in under a week. Short little fluff with Dean and Cas acting like ridiculous dorks in love. Minor spoilers for season 10 at end. Destiel Dean X Cas [NEW CHAPTER WITH GABE X SAM ADDED]
1. Dean

**Hiya guys! This is a quick one shot- just Dean fooling around and flirting. Angel Cas, human Dean, set around season five. Also, if you haven't checked it out yet, I have a story up in progress called Four Letters, and I would love it if you would check that out!**

 **Still got no ownership of any of this- or Cas and Dean would be together.**

"Hey there Cas." Dean leaned against the wall, smirking.

Cas looked up from the book he was staring at. "Oh, hello Dean." He responded. "I did not expect to see you there."

"I was just wondering…" Dean casually examined his fingernails. "Did it hurt?"

Cas tilted his head. "Did what hurt Dean? Are you referring to when I rested my hand on the hot burner earlier today, Dean? You need not worry- I have informed you that I heal very quickly. This is just a vessel." He smiled a little bit.

Dean let out a small chuckle. "Not quite what I was going for, Cas."

"Then what were you referring to?" Cas frowned, slightly agitated that he did not understand all of these human things. "Oh! Dean is this a flirtation?" Cas' eyes lit up. "I read all about those!"

"Uh…" Dean looked at him. "When did you read about this?"

"Sam showed me several of the books in your library. They were quite educational, Dean."

Dean's eyes widened slightly. "Cas tell me, what books did he show you?"

"He lead me towards books such as _The Velvet Promise, Twilight, New Moon, Eclipse,_ and _Breaking Dawn_ " Cas beamed happily. "I must say, I thoroughly enjoyed most of them."

Dean let out a strangled groan. "Oh, no Cas. He introduced you to trashy romance novels!"

"I do not find them trashy, Dean. I must now go assist Sam in the library" Cas's words were punctuated with him standing up gracefully. "Watch your words." There was a quick flutter, and Cas was gone.

•-•

Cas could hear footsteps, and he turned around, but stayed on the couch. Dean was leaning in the doorway again. "If you have come to, as you put it, trash my style, I want to hear nothing of it." Cas wrinkled his nose.

"No, no no, Cas I was simply wondering. If you and two other angels had a threesome, would you, ya know, be a triangel?" Dean was grinning widely, apparently very pleased with himself for coming up with this.

"You have to be straight to be part of a triangle, Dean." Cas pointed out, making a big deal of turning another page in his book, _Bloodlines_.

"Really Cas? More vampire novels?" Dean threw his hands in the air, and Cas could hear him clomping away.

Sam peeked his head around from the kitchen. "He trashed your novels?" He asked bitterly.

"Yes."

•~•

Cas hummed along to the music coming from the small box near the stove as he pushed bread into the toaster. He was too scared to attempt to use the stove again, so Sam had recommended he wait for Dean. However, Sam had reassured Cas that very little could go wrong if he attempted to utilize the toaster, so here Cas was, trying to surprise Dean with a nice breakfast.

Dean walked into the kitchen then, rubbing his eyes. He saw the back of his angel, and heard the surprisingly in tune humming. "Mornin' Sunshine." He cracked a sleepy smile at him as Cas turned around.

"Hello Dean." Cas smiled at him. "I'm making you breakfast."

"Well isn't this a pleasant surprise." Dean chuckled. "Just one thing."

"Yes, Dean?"

"Wouldn't that be 'Halo, Dean,' instead of 'Hello Dean,'?" Dean smirked.

Cas just stared at him.

"Halo from the other sideeeee…" Dean sang off key to the music.

Cas had just turned around again, deciding to ignore Dean, when the toast decided to pop out. Cas fell back with a scream.

Dean flew out of his chair, and was at Cas' side in an instant.

"You didn't tell me they flew out!" Cas whimpered slightly.

•~•

Dean walked down the hall to Cas' room, peeking in at the angel. He lay there, wide awake, in his bed.

"Dean." Cas' deep voice rang out, and Dean jumped slightly. He wasn't expecting Cas' eyes to be open even if he was mimicking sleep.

"Why do you try to sleep?" He asked his angel, sincerely curious.

"To try and feel what humanity feels again." Cas sat up. "You remember when I was human, right Dean?"

"Of course."

"There were some aspects of that life that I enjoyed. Sleep happened to be one of them." Just then, Cas looked Dean dead in the eye. "However, like the angels, the aquatic creatures on this planet do not need sleep. Why is that any different from humans? Surely they are not tired?"

The ghost of a smile tugged at Dean's lips. "I guess that would make you an angelfish then."

"Dean." Cas stared at him. "That one doesn't make any sense at all. I bear no resemble to any kind of fish."

Dean sighed. "It's too late for this shit. I'm going to bed. See you in the morning, Sunshine."

"Goodnight Dean."

•~•

Cas was sitting on the couch, big headphones on his ears. He looked up as Dean walked into the room, reluctantly pulling them off. "Hello Dean."

"Hey Cas, whatcha listening to?"

"It is a new musical that Sam has introduced me to. I believe it is called 'Hamilton'."

"Really?" Dean wrinkled his nose. Finally he sighed. "Well, Sammy tried to introduce me to that one once too. How are you liking it?"

"I am really enjoying it!" Cas' eyes sparkled with passion as he explained to Dean, "The songs are pleasing rhythmically and the beats are dropped rather nicely!"

"I think you got some sayings mixed up in there Cas." Dean chuckled.

"The storyline is also amazing. My favorite of the characters is the eldest of the Schuyler sisters." Cas continued.

"You mean, ANGELica?" Dean smirked.

"I thought you did not like the Hamilton soundtrack, Dean?" Cas replied without missing a beat.

Dean's face paled.

•~•

Cas and Dean sat snuggled next to each other on the couch, a crappy horror movie on. Dean popped another piece of popcorn into his mouth.

"So Cas, What do you think? This one gory enough for you?"

"Dean, after what we see in our day to day lives, I fail to see how this would invoke fear in the hearts of men and women alike." Cas frowned slightly.

"Most people aren't like us, Cas. Oh look! They found another dead one!" Dean pointed at the screen excitedly.

"Oh dear, this one seems to have gotten his abdominal region torn open." Cas commented dryly.

Dean chuckled. That was the real reason he loved watching crappy horror films with Cas. This and just being near him.

"Yeah, Cas. This one seems to have gotten himself pretty badly mANGELed." Dean barely managed to keep a straight face when he said this.

Cas turned to him.

There was a moment of silence, and then just, "God damn it Dean…"

Another moment.

"I love you."

Cas leaned in and kissed Dean on the lips. "Never forget, I might be the one with wings, but you're the real angel here."

BONUS:

Dean sat tied to a chair, his eyes jet black. Smirking, his eyes shifted from Cas to Sam and back again. "Let me out of this chair now, or there will be consequences, angel." He purred slightly.

"I don't think you're in any position to be making DEMONds right now, Dean." The words were out of Cas' mouth before he could stop them.

"Really Cas? Puns? Now you get them?" Dean stared at him for a moment before uttering three more words. "Cain you not?'

Cas cracked a tentative grin at him. "I don't think I'm Abel to." He would cure Dean, whatever it took. And once he had, Dean would be back to normal. At least, as normal as it could get with all of the pun yet to come in their future.

 **Yes it is short, and yes I am sorry. For all you wondering, I am still continuing Four Letters, I just got caught up in midterms. This is a little something I've had lying around for a while, so I decided to post it. I'm also working on another much longer Dean X Cas story (Probably at least over 10k, and have been trying to finish and get that up for all of you guys. Please read/review! Love you all!** **3**


	2. Gabe

**Hey everyone! I needed to take a little break from Four Letters right now, so I decided to make this little monstrosity. Cause who doesn't need to see me floundering to give you guys silly puns? Set during EARLY season 13, if Gabe had been with them. Just… since it's Sabriel, it's obviously more dirty. I just didn't want to change the rating. So take caution. :)**

•~•~•~•~•

"Hey, Samsquatch!" Gabe was lying on his back across the pool table they owned, staring at Sam's ass as he moved throughout the kitchen. "Cas and Dean are gone, want to…" He trailed off suggestive, winking at Sam.

Sam turned to look at him strangely. "Gabe. Dinner."

"But Sammmyyyyy…" Gabe whined, sticking a brigt red lollipop into his mouth and sucking on it.

Sam rolled his eyes and walked over to Gabe, squatting down to his level and looking into his honey golden eyes. "Dinner." He whispered.

As Sam made to stand up, Gabe grabbed his collar. "No, don't leave me! Not without a goodbye kiss! I've been so lonely without you..."

Sam rolled his eyes. "Fine." He slowly pulled Gabe's mouth to his, kissing him thoroughly and tantalizingly. When they finally parted, they were both breathing hard.

"Gee, Sammy, you give me _moose_ bumps when you do that." Gabe smirked at his boyfriend, pleased with himself.

Sam got up and left the room.

"Sammy, come on, wait! It was a little funny, right?"

Another moment of silence.

"Sammy?"

•~•~•~•~•

There was a tense silence, as Dean and Sam stood, just staring at each other. Dean's jaw was set, Sam's hands angrily balled into fists. This was not the first time they had argued about this, but both of them had been yelling at each other for a while now, and had just stopped.

Sam broke the cautious silence once more. "He's not a monster, Dean."

"Well you don't know if he'll go darkside. I'm just saying, when he does, I'll have to be there to deal with him, because you can't kill the spawn of Lucifer."

"Dean, he's so much more than that! Jack has the potential to be good. He doesn't have to be like Lucifer!"

"But-"

Dean's remark was interrupted by Gabe walking through the room, stuffing doughnuts into his face. "Awkward…" He muttered through the doughnut. "Dean, Sammy's pretty una _moose_ d right now, I suggest backing off until he's a little happier."

Sam left the room.

"Is that all you came through here to do?"

"Well, make that master pun and let you know the kid's been listening to everything you've been saying. He's right over there. Ciao!" Gabriel walked through, and continued stuffing doughnuts into his mouth as fast as he could.

"Shit." Dean breathed out.

•~•~•~•~•

Cas and Sam were discussing ways that Jack's powers might work, and the mysterious rift to another dimension that he had summoned, when Sam suddenly felt tiny fingers combing through the silky back of his head of hair.

He almost jumped a foot in the air, even after he realized that it was Gabriel. "Gabe!" Sam gasped out as Cas shuffled awkwardly. "What are you-did you climb me like a tree?"

A muffled "Maybe" could be heard as Gabe buried his face in the back of Sam's hair. Sam shook his head fondly. "Something you need, Sugar?"

"Oh, I just wanted to know how you got your hair so smooth and silky." Gabe leaned over Sam so that his chin rested on his shoulder. "Do you use a certain kind of gel? Or maybe…"

Oh no. Sam could hear it already. He was gonna say it.

"Is it a particular mousse that you use?" He said it. And from the way he was smirking at incorporating the word _moose_ into normal conversation without it being a pun, he was very pleased with himself about it.

Sam sighed heavily, shrugging Gabriel off of his shoulders, and left the room.

•~•~•~•~•

Sam walked into the bathroom a few days later, trying to grab the nail clippers. The sight that greeted his eyes had him blinking in astonishment. "Dude." He looked at the man he loved, and you could almost see the gears in his head turning as he rethought every aspect of his life. Gabe was stuck in a position between standing and squatting on top of the sink in front of their mirror, and appeared to be sticking his face onto the mirror. "You ok?" He asked tentatively.

Gabe whipped his head around from where he was admiring himself in the mirror, and Sam recoiled in fear for a moment before his eyes fully processed what he was seeing. "Heya Sammy! What do you think? Do you like it?" Gabriel was sporting a giant mustache. He was also grinning from ear to ear. "I grew it just for you! Thought it would feel nice when we kiss." Gabe puckered his lips, and Sam honestly couldn't tell if he was joking or not.

"When did you have time to grow a mustache?" Sam was astonished, but not as much as he would have been if it were anyone but Gabriel.

"It's not a _must_ ache, Sammy! It's a _moose_ stache!" Gabe pouted. "See? They're like little antlers!"

Sam left the room.

•~•~•~•~•

Jack and Sam were listening to music together in the kitchen when Gabe sauntered into the room again. He was holding a tub of frosting, licking one of his fingers as he did. He paused to give Sam a quick kiss on the cheek as he walked past, finally settling himself down next to Jack.

"So." He started. "Pitch Perfect."

Sam barely looked up from the dough he was mixing. "So? Jack likes it."

Jack's huge smile seemed to light up the whole kitchen as he continued tapping out the beat to the cup song. "I do enjoy it."

"How'd you guys even find that thing? It's like… a bajillion years old." Gabe chuckled.

"Surfing Netflix." Was Sam's response.

The kitchen was quiet a moment more, save for Anna Kendrick singing in the background. Finally, Gabriel began to sing along. It started out quiet, but grew in volume until he was belting out the words. "You're gonna _moose_ me everywhere, you're gonna _moose_ me when I'm gone!" He was singing his heart out.

Sam left the room.

•~•~•~•~•

Sam was lifting weights this time when Gabriel walked into the room. "Oh, hey Gabe. Can you help spot me quick? I want to-"

Gabe was practically drooling. "Anything to see your beautiful _moose_ les, Sammy.

Sam stood there a moment. Finally, he looked back at Gabe. "You know, I would leave, but I really need to get these reps in."

Gabe took that as a silent victory, even as he watched Sam's arms go up and down, the heavy bar lifting into the air and coming back down again. It took a very long time before Sam's breathing became labored, and with Gabe's help, he slowly put the bar back into its place.

Sitting up, he looked over at Gabe. all was silent for a moment, then-

"I'm _moose_ tly ok with your stupid jokes by now."

Gabe turned to Sam, his eyes shining. "Oh, I knew you were the one!" He flew at him in a tackle hug, and they both hit the floor, hard.

"Ouch... " Sam rubbed his back slightly as he stood up.

"Sorry," Gabriel said sheepishly as he stood up as well. "I love you."

Sam just smiled a little bit. And then he left the room.

Gabe's distraught cry of, "Oh, come on!" was acknowledged with a simple chuckle.

•~•~•~•~•

 **So that's that monstrosity. I am so sorry. I'm pretty sure it's the worst piece of writing I've ever done. XD I do like it though, in a twisted, motherly way. I hope you enjoyed this installment in the previously thought to be completed series.**


	3. Jack

**Hello again everyone! Bet you didn't see this coming! :P I'm back with a slightly different story here, since I can't focus my brain on Four Letters right now. So enjoy Jack trying his hand at puns! (EVERYONE IS HAPPY, EVERYTHING IS GOOD.) Bit more of a Crack Fic, but if that's how it goes, that's how it goes. And it's not like it wasn't already.**

~•~•~•~•~

They were sitting around the main table in the bunker when it happened. They were all sitting around, and Gabe was talking nonstop, using vivid gestures. He was sitting on Sam's lap, and Sam had his hands wrapped tightly around the smaller man's waist. Cas had his head on Dean's shoulder, and the green eyed man was leaning slightly into him as well, a small smirk on his face.

"She was flirting with me, right? When I tried to tell her I was taken, she started to get nasty. And so I said, 'Woman, you're such a bitch! I'm a taken man,' and then I ran home to you, Sammy!" Gabe made kissy lips at Sam, who chuckled at the anticlimactic resolution to such a built up story.

"I guess you could say she was… barking up the wrong tree." Jack tried after a short silence, smiling innocently. He had just begun to understand idioms, and he was quite pleased with himself.

All other parties turned to stare at him, horrified.

"Which one of you taught him puns?" Cas was distraught.

"No, kid, just… no." Dean shook his head. "That's not how you do it!" Cas shot him an angry look, and his hands went up defensively. "What? I didn't teach the kid anything like that! It wasn't even that good of a pun!"

Sam frowned. "I think that's part of the reason Cas is so upset, Dean." They all turned to the trickster.

"What? Why do you all turn to me whenever something like this happens?" Gabe cried out, his hands flying up defensively as well. "I'm always the victim!"

"Because you're the only one dumb enough to try and teach the kid puns." Dean growled out.

"Fair point, fair point." Gabe frowned. "I didn't do it though."

"Kid, where did you learn-" Dean turned back to look at Jack, but he was already gone. "The hell-?" He muttered.

Sam shrugged.

~•~•~•~•~

"Come on, Dean-O, stop yelling!" Gabe whined, his tongue sticking out as he clutched the wii remote slightly harder.

"I am in third, and you just expect me to calm down!?" Dean roared, trying his hardest to work his way back up the ranks. "I was in first, Gabe! First!"

"On second thought, maybe getting them Mario Kart was a bad idea…" Gabe leaned over, whispering to Cas and Jack.

Cas acknowledged this with a quick nod of the head, leaning over and patting Dean's shoulder, but Jack was zoned out, his focus rapt and on the TV.

Dean growled once more. "Ok, good. Back in first."

Jack smiled slightly, the power up block that he had just hit flipped to reveal a red shell. Dean saw it out of the corner of his eye, and he let out a string of curses, hitting another power up block. Coins.

"Shit!" He exclaimed as Jack shot him, racing on ahead of him across the finish line. "I lost again! How are you so good at this? You weren't even created yet when this game was made!"

"Geez Dean, don't be so pessimistic. If Jack is good at video games, just let it happen. It happens to all other fathers, you don't need to be so upset." Sam frowned slightly, even though he was slightly miffed as well that Jack could beat them all so easily.

"It's ok Sam, I understand. It's just in his blood." Jack turned to Sam, smiling that innocent smile again.

"In his… blood?" Sam was confused.

"Yes, Be negative." Jack sat there a moment, waiting for his pun to sink in. Maybe this time they would like it!

There was a chorus of groans from around the room, starting with Dean, moving all the way to Castiel, who put his head in his hands in despair. He had hoped to shield Jack from this life, but it seemed far too late for that. Two puns in two days, he knew that that couldn't be a coincidence.

"Jack, how did you do that?" Sam asked him, choosing his words carefully.

"Oh, I simply found a word or phrase that seemed to have a double meaning, and waited until the situation seemed fit to say it. I have been observing all of you these past few weeks, and seeing as you all seem to treat them as conversation starters and chuckle when they are said, I decided to learn how to as well!" Jack smiled at them, proud of himself. "The internet came in handy."

Dean rubbed soothing circles on Cas' back sympathetically as the angel tried his best to keep his composure intact.

"Ok, Jack. Puns aren't… funny." Sam tried to explain. "If people use them too much, or too often, they aren't received very well. People kind of hate them."

Jack looked at him in confusion. "But you, Dean, and Gabe use them all the time." He turned to Cas. "Even you, Castiel. You as well are guilty of this."

Cas hung his head in shame. "While this may be true, Jack, I hoped that you would not fall victim to this disease as well. I at least hoped you would be older."

"Huh." Was all Jack said. There was a long silence, and then, "Can we at least keep playing? I was on a roll."

"Jack!"

Jack let out a small chuckle, turning once more to the television. He didn't miss Dean muttering to Cas, "This is getting _punbearable…_ "

~•~•~•~•~

Jack was doing his best to make tea for Sam, who's throat was bothering him recently. He had boiled the water, and put the tea and honey in, just as Dean had instructed. Carefully, balancing the steaming tea in one hand, he made his way into Sam's room.

Sam looked up from his computer, sucking on a cough drop. "Oh, hey Jack." His words were slightly raspy sounding, and punctured by a small fit of coughing.

"I made you tea." Jack smiled sweetly, holding out the steaming cup for Sam to take. "I hope you like it. Dean said honey helps with coughing, so I put some in as well."

The hint of a smile tugged at Sam's lips as he took the cup, looking inside. "Thanks Jack, but I can't drink this."

Jack was perplexed. "But Dean and Cas insisted that it would help to battle your cold?" He spoke as if that sentence was a question, and Sam chuckled slightly before more coughing impeded his speech.

"Jack, when you make tea, you can't just put the tea leaves in." Sam explained. "When I'm better-" he coughed a little, "-I'll teach you how to, ok?"

Jack nodded slowly. "Well you know what they say. If at first you don't succeed, chai, chai again."

Sam stared at him, distraught. "Is it Gabe? Is Gabe the one telling you to do this?"

"No, I simply wanted to fit in." Jack looked him over. "I will prepare you a better cup of tea." Jack left the room.

~•~•~•~•~

Cas and Jack were preparing lunch for everyone in the bunker, as they had been doing of late. Jack was pulling out lettuce for Sam's salad when Cas spoke. "I do wish that Dean would decide to eat healthier."

Jack turned around. Cas was staring at the calories on the back of the bacon in distress. "Well, you know successful diet hinges on mind over platter." The ghost of a smile tugged at his lips as he evaluated Castiel's reaction.

"Yes, but to get him on a diet…" Cas muttered, distracted. Suddenly he whirled around. "Wait a moment!"

"Yes?" Jack looked over at him innocently, pulling out tomatoes to put on Sam's salad.

Cas sighed, opting for the 'nice dad' approach. "What has possessed you to speak as such, Jack?"

"I was up late reading on the internet." Jack confessed, continuing to pull out vegetables. "I just want to be like you guys."

Cas smiled as Dean, Sam, and Gabe walked into the room. "Is that bacon I smell?" Dean grinned. "Yum. You're the best, Angel."

"Don't _hog_ all of the bacon, Dean! Leave some for me!" the words were out of Gabe's mouth before he could stop them.

"Gabe!" Sam was aghast. "We said we'd stop telling puns!"

Dean finally sighed, giving in to the pun. "Stop your _swining_ , Sammy."

Jack leapt on his chance, tacking on his favorite pork related pun. "Yeah, that's utter _hogwash,_ and you know it!"

"Will everyone stop _shoating_?" Cas groaned. "These puns are really quite terrible."

"I am full of _gilt_. I'm so sorry, Sammy. I never meant for it to end this way!" Gabe added in dramatically, referring to the pun that started this all.

Dean blinked. "Ok, now all of these pig puns are flying over my head."

"A gilt is a female pig under one year old," Jack added in helpfully for Dean's benefit.

"Enough, please!" Sam cried out, distraught. "Did you forget about Jack?"

At least Cas and Dean had the courtesy to look guilty. Gabe just chuckled. "The kid's good at it Sammy. I don't see why we'd try and shelter him from it any longer. Cat's out of the bag. Hell, I don't think the cat was ever _in_ the bag.

There was a moment of silence.

"I'd like my salad now."

~•~•~•~•~

They were all gathered around the table, eating lunch. No one had spoken since, except some muttering between Sam and Gabe in the corner. Finally, Sam stood up, his fork with salad on it still in hand.

"May I have your attention?" Sam spoke out to them all, Gabe staying seated beside him.

"Sam, please, we don't-"

"No, Cas, _lettuce_ speak." Gabe frowned at him.

Jack leaned over to Dean and whispered, "Yeah, well then it must be a big _dill._ "

Dean cracked up laughing, leaning back. "I think you'd _butter_ stop doing that, or someone's gonna get mad."

Cas gave Dean a mischievous look. " _Honey,_ come on..."

"Please, give me thirty seconds!" Sam was ticked off. Finally, he turned to Gabe, doing the one think he knew would get their attention. "It's like they don't _carrot_ all."

Jack, Cas, and Jack looked at him in shock. "Ok, you have intrigued us. Please, dazzle us with your pun laden speech."

Sam took a deep breath. "Frankly, I don't give a _ham._ You seem intent on raising Jack in a pun rich environment, and since I love _olive_ you, I will agree to your wishes, on one condition." Sam paused. "Jack is the only one allowed to start the punning. From there, you can tack on any puns that you want, but it has to start with Jack. Fair?"

They all nodded and muttered, turning to Jack, who was grinning broadly. "Sam, that was an _amaizing_ speech. Thank you." He looked around at them all. "And I want you all to know that _olive_ you too."

Sam just smiled at Jack, shaking his head slowly. "I have got to say, Jack, you have got a real _snack_ for these puns."

Jack hadn't grinned this much in a very long time.

~•~•~•~•~

 **So that's it! I might add more in the future, (since I do have some ideas :3) but for now, have a great night! I hope you enjoyed! Please leave a review and let me know what you thought!**


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